I'm not an expert(probably the second dumbest on the the boards) and someone will probably correct/critique this post. Which is fine by me!
I've been throwing 500 a month into the SPYV(Yes, I know SPY is better for dividend yield. UGH! Whatever...

) for 6 years now, 3000 a month the last 2 years. I don't know enough nor have worked out a system to throw it all into individual stocks.
Between investing that and dividend re-investing, I'm dollar cost averaged out at about 91. It's trading at 103 as of today. I put another 1500 in this afternoon. The math and past performance says it'll all work out. When it goes down, that's even more shares. When it goes back up, $$$$. Love love LOVE indexes that track the market when your in the learning phase. It will still make you money while you figure out how to properly make more than the market with individual stocks.
Like others have said, it's really never a bad time to get into an S&P 500 index. You can always dollar cost average down while it dips and dividend re-investment is still growth(I would almost argue, most of your growth, just taking a glance at how it performed for me). In my mind...
That being said, I threw 20k at a biofuel company a year ago and it made me about 40k a year later, yesterday actually. Pulled out of it this morning, "HI-OOOH". I didn't realize at the time that their management was so awful, so I'm out. Maybe it'd make me a fortune much later, given their product, but that is a highly speculative and risky investment that I'm not comfortable with having such a large % of my money in. Might buy back in with a more appropriate amount when it surely dips next week. I'm confident in their product, just not the company. You get lucky betting on red sometimes. Calculated Investing is better and the "idiots ETF" does work OK IMO.
VWLEX seems to have done pretty well for people I know that are into that. They aren't accepting new investors as of at least today though.
Oh, and debt is a tool! I learned the hard way